Study Of Photoredox-Catalyzed Sulfenylation/Cyclization Of N-aryl-N-tosylpropargylamine

Oganosulfur compounds are important organic intermediates in organic synthesis.Owing to their unique biological activities and chemical properties.They have received extensive attention from industry in the development of new materials and new drugs.Therefore,the development of a novel and effective the C-S bond formation method is a challenging subject.The traditional methods for the formation of C-S bond depend on the transition-metals-catalyzed cross-coupling or the direct sulfenylation under metal-free conditions..In recent years,visible light catalysis has attracted more and more attention from chemists due to its advantages such as simple operation,mild conditions and environmentally friendly.Therefore,the direct construction of C-S bond through visible-light catalysis has gradually become an important and challenging method.In this paper,N-aryl-N-tosylpropargylamine and disulfides following a cyclization/detosylation/aromatization cascade reaction via photoredox catalysis was studied.The full text is divided into three parts:The first chapter summarizes the reaction types and related mechanisms of the reaction of introducing thioaryl groups,and introduces the development history,research progress and the corresponding new synthetic methods of sulfenylation in recent years.The second chapter introduces the historical background and reaction process of visible light catalysis,and introduces the design,selection and influencing factors of the catalysts.The third chapter mainly introduces a tandem cyclization/sulfenylation/detosylation/aromatizationreactionofavisible-lightcatalyzed N-aryl-N-tosylpropargylamine and p-tolyl disulfide.It was studied under mild conditions,using 1,2-dichloroethane as solvent,adding twice amount of anhydrous potassium phosphate as base.The reaction was irradiated for 48 hours,and a series of3-phenylthioquinoline and its derivatives were produced under the visible-light catalysis.At the same time,we investigated the applicability of the substrate and proposed a reasonable reaction mechanism through the relevant verification experiments.The structure of the product was determined by ¹H NMR,¹³C NMR and high resolution mass spectrometry.This paper is different from the traditional method of introducing thioaryl substituents,and studied the visible-catalyzed tandem cyclization thiolation reaction,and synthesized sulfur-containing nitrogen heterocyclic compounds with important application value.